Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CCCNc1nc(Nc2cccc(F)c2)ncc1-c1cc(CCN2C(=O)c3ccccc3C2=O)no1
InChiKey
OLXUBJIIUWEJEQ-UHFFFAOYSA-N
Route Signature
b3f855fd42a01c64c13afd5e762e43ea5046096c7038dc0ff9a54567be15c82d
Synthesis route with 7 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_8e3f44fee898933583c9de3e",
"signature": "b3f855fd42a01c64c13afd5e762e43ea5046096c7038dc0ff9a54567be15c82d",
"contentHash": "5a758bf8f316583331602b70ca1bef33ab48185e71b189c11b76f3cbb4472708",
"length": 7,
"isConvergent": false
},
"target": {
"id": "sa_f95490fc937b3830469b14a0",
"benchmarkSetId": "61e696668b63e77d7c2a29c0821768e1c383de8313852d6e995224859494442e",
"targetId": "n5-00064",
"moleculeId": "sa_a21db9066dc78c4dbed26609",
"smiles": "CCCNc1nc(Nc2cccc(F)c2)ncc1-c1cc(CCN2C(=O)c3ccccc3C2=O)no1",
"routeLength": 7,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_a21db9066dc78c4dbed26609",
"inchikey": "OLXUBJIIUWEJEQ-UHFFFAOYSA-N",
"smiles": "CCCNc1nc(Nc2cccc(F)c2)ncc1-c1cc(CCN2C(=O)c3ccccc3C2=O)no1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "12290",
"routeId": "sa_8e3f44fee898933583c9de3e",
"moleculeId": "sa_a21db9066dc78c4dbed26609",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_a21db9066dc78c4dbed26609",
"inchikey": "OLXUBJIIUWEJEQ-UHFFFAOYSA-N",
"smiles": "CCCNc1nc(Nc2cccc(F)c2)ncc1-c1cc(CCN2C(=O)c3ccccc3C2=O)no1"
},
"smiles": "CCCNc1nc(Nc2cccc(F)c2)ncc1-c1cc(CCN2C(=O)c3ccccc3C2=O)no1",
"reactionStepId": "sa_25a157041a684324b71bd179",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150045339A1;1471;1653024\",\"rsmi\":\"O[CH2:23][CH2:22][c:21]1[cH:20][c:19](-[c:18]2[c:5]([NH:4][CH2:3][CH2:2][CH3:1])[n:6][c:7]([NH:8][c:9]3[cH:10][c:11]([F:12])[cH:13][cH:14][cH:15]3)[n:16][cH:17]2)[o:36][n:35]1.[NH:24]1[C:25](=[O:26])[c:27]2[cH:28][cH:29][cH:30][cH:31][c:32]2[C:33]1=[O:34]>C1CCOC1.CC(C)OC(=O)N=NC(=O)OC(C)C.Cc1ccccc1.c1ccc(P(c2ccccc2)c2ccccc2)cc1>[CH3:1][CH2:2][CH2:3][NH:4][c:5]1[n:6][c:7]([NH:8][c:9]2[cH:10][c:11]([F:12])[cH:13][cH:14][cH:15]2)[n:16][cH:17][c:18]1-[c:19]1[cH:20][c:21]([CH2:22][CH2:23][N:24]2[C:25](=[O:26])[c:27]3[cH:28][cH:29][cH:30][cH:31][c:32]3[C:33]2=[O:34])[n:35][o:36]1\"},\"mapped_reaction_smiles\":\"O[CH2:23][CH2:22][c:21]1[cH:20][c:19](-[c:18]2[c:5]([NH:4][CH2:3][CH2:2][CH3:1])[n:6][c:7]([NH:8][c:9]3[cH:10][c:11]([F:12])[cH:13][cH:14][cH:15]3)[n:16][cH:17]2)[o:36][n:35]1.[NH:24]1[C:25](=[O:26])[c:27]2[cH:28][cH:29][cH:30][cH:31][c:32]2[C:33]1=[O:34]>C1CCOC1.CC(C)OC(=O)N=NC(=O)OC(C)C.Cc1ccccc1.c1ccc(P(c2ccccc2)c2ccccc2)cc1>[CH3:1][CH2:2][CH2:3][NH:4][c:5]1[n:6][c:7]([NH:8][c:9]2[cH:10][c:11]([F:12])[cH:13][cH:14][cH:15]2)[n:16][cH:17][c:18]1-[c:19]1[cH:20][c:21]([CH2:22][CH2:23][N:24]2[C:25](=[O:26])[c:27]3[cH:28][cH:29][cH:30][cH:31][c:32]3[C:33]2=[O:34])[n:35][o:36]1\"}",
"reactionStep": {
"id": "sa_25a157041a684324b71bd179",
"reactionHash": "47e4a7c7013b1e3a2e606373079f671bf5bd88c12c30ae1920950b416e2f3152"
},
"children": [
{
"id": "12291",
"routeId": "sa_8e3f44fee898933583c9de3e",
"moleculeId": "sa_455199aec8cd5cc81c72fd6e",
"parentId": "12290",
"isLeaf": false,
"molecule": {
"id": "sa_455199aec8cd5cc81c72fd6e",
"inchikey": "FALUUNJWZKMHNI-UHFFFAOYSA-N",
"smiles": "CCCNc1nc(Nc2cccc(F)c2)ncc1-c1cc(CCO)no1"
},
"smiles": "CCCNc1nc(Nc2cccc(F)c2)ncc1-c1cc(CCO)no1",
"reactionStepId": "sa_e24d12a19920e106402da74b",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150045339A1;1468;1653023\",\"rsmi\":\"CC(C)(C)[Si](C)(C)[O:24][CH2:23][CH2:22][c:21]1[cH:20][c:19](-[c:18]2[c:5]([NH:4][CH2:3][CH2:2][CH3:1])[n:6][c:7]([NH:8][c:9]3[cH:10][c:11]([F:12])[cH:13][cH:14][cH:15]3)[n:16][cH:17]2)[o:26][n:25]1>C1CCOC1.CCCC[N+](CCCC)(CCCC)CCCC.CCOC(C)=O.O=C(O)O.F.[Na+]>[CH3:1][CH2:2][CH2:3][NH:4][c:5]1[n:6][c:7]([NH:8][c:9]2[cH:10][c:11]([F:12])[cH:13][cH:14][cH:15]2)[n:16][cH:17][c:18]1-[c:19]1[cH:20][c:21]([CH2:22][CH2:23][OH:24])[n:25][o:26]1\"},\"mapped_reaction_smiles\":\"CC(C)(C)[Si](C)(C)[O:24][CH2:23][CH2:22][c:21]1[cH:20][c:19](-[c:18]2[c:5]([NH:4][CH2:3][CH2:2][CH3:1])[n:6][c:7]([NH:8][c:9]3[cH:10][c:11]([F:12])[cH:13][cH:14][cH:15]3)[n:16][cH:17]2)[o:26][n:25]1>C1CCOC1.CCCC[N+](CCCC)(CCCC)CCCC.CCOC(C)=O.O=C(O)O.F.[Na+]>[CH3:1][CH2:2][CH2:3][NH:4][c:5]1[n:6][c:7]([NH:8][c:9]2[cH:10][c:11]([F:12])[cH:13][cH:14][cH:15]2)[n:16][cH:17][c:18]1-[c:19]1[cH:20][c:21]([CH2:22][CH2:23][OH:24])[n:25][o:26]1\"}",
"reactionStep": {
"id": "sa_e24d12a19920e106402da74b",
"reactionHash": "6dfbba130b0bf17b29c1ceef9563d7cb4f5c8c3ff7fd08b187c5baaf7b2ba0dc"
},
"children": [
{
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"routeId": "sa_8e3f44fee898933583c9de3e",
"moleculeId": "sa_9ec57145eaf747b8a0b60d88",
"parentId": "12291",
"isLeaf": false,
"molecule": {
"id": "sa_9ec57145eaf747b8a0b60d88",
"inchikey": "JDSFOLPTIRHJJB-UHFFFAOYSA-N",
"smiles": "CCCNc1nc(Nc2cccc(F)c2)ncc1-c1cc(CCO[Si](C)(C)C(C)(C)C)no1"
},
"smiles": "CCCNc1nc(Nc2cccc(F)c2)ncc1-c1cc(CCO[Si](C)(C)C(C)(C)C)no1",
"reactionStepId": "sa_7a5891d30a2cddd621c90afe",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150045339A1;1465;1653022\",\"rsmi\":\"O=[N+:32]([CH2:21][CH2:22][CH2:23][O:24][Si:25]([CH3:26])([CH3:27])[C:28]([CH3:29])([CH3:30])[CH3:31])[O-:33].[CH3:1][CH2:2][CH2:3][NH:4][c:5]1[n:6][c:7]([NH:8][c:9]2[cH:10][c:11]([F:12])[cH:13][cH:14][cH:15]2)[n:16][cH:17][c:18]1[C:19]#[CH:20]>CCN(CC)CC.CCOC(C)=O.Cc1ccccc1.O.O=C=Nc1ccccc1>[CH3:1][CH2:2][CH2:3][NH:4][c:5]1[n:6][c:7]([NH:8][c:9]2[cH:10][c:11]([F:12])[cH:13][cH:14][cH:15]2)[n:16][cH:17][c:18]1-[c:19]1[cH:20][c:21]([CH2:22][CH2:23][O:24][Si:25]([CH3:26])([CH3:27])[C:28]([CH3:29])([CH3:30])[CH3:31])[n:32][o:33]1\"},\"mapped_reaction_smiles\":\"O=[N+:32]([CH2:21][CH2:22][CH2:23][O:24][Si:25]([CH3:26])([CH3:27])[C:28]([CH3:29])([CH3:30])[CH3:31])[O-:33].[CH3:1][CH2:2][CH2:3][NH:4][c:5]1[n:6][c:7]([NH:8][c:9]2[cH:10][c:11]([F:12])[cH:13][cH:14][cH:15]2)[n:16][cH:17][c:18]1[C:19]#[CH:20]>CCN(CC)CC.CCOC(C)=O.Cc1ccccc1.O.O=C=Nc1ccccc1>[CH3:1][CH2:2][CH2:3][NH:4][c:5]1[n:6][c:7]([NH:8][c:9]2[cH:10][c:11]([F:12])[cH:13][cH:14][cH:15]2)[n:16][cH:17][c:18]1-[c:19]1[cH:20][c:21]([CH2:22][CH2:23][O:24][Si:25]([CH3:26])([CH3:27])[C:28]([CH3:29])([CH3:30])[CH3:31])[n:32][o:33]1\"}",
"reactionStep": {
"id": "sa_7a5891d30a2cddd621c90afe",
"reactionHash": "f85512fee49aec65a24198d33ae2ca13c7efa9fe48c5e3ab2b30188d28123e58"
},
"children": [
{
"id": "12293",
"routeId": "sa_8e3f44fee898933583c9de3e",
"moleculeId": "sa_e2d286f785ac9d18bd25c1f4",
"parentId": "12292",
"isLeaf": true,
"molecule": {
"id": "sa_e2d286f785ac9d18bd25c1f4",
"inchikey": "SSOPRAUEQPLFKT-UHFFFAOYSA-N",
"smiles": "CC(C)(C)[Si](C)(C)OCCC[N+](=O)[O-]"
},
"smiles": "CC(C)(C)[Si](C)(C)OCCC[N+](=O)[O-]",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "12294",
"routeId": "sa_8e3f44fee898933583c9de3e",
"moleculeId": "sa_f41c02a5b6b81b08c7e8758e",
"parentId": "12292",
"isLeaf": false,
"molecule": {
"id": "sa_f41c02a5b6b81b08c7e8758e",
"inchikey": "ZFQIWACUYPQMDS-UHFFFAOYSA-N",
"smiles": "C#Cc1cnc(Nc2cccc(F)c2)nc1NCCC"
},
"smiles": "C#Cc1cnc(Nc2cccc(F)c2)nc1NCCC",
"reactionStepId": "sa_fb9584cb61f5472966300676",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150045339A1;1462;1653021\",\"rsmi\":\"C[Si](C)(C)[C:1]#[C:2][c:3]1[cH:4][n:5][c:6]([NH:7][c:8]2[cH:9][c:10]([F:11])[cH:12][cH:13][cH:14]2)[n:15][c:16]1[NH:17][CH2:18][CH2:19][CH3:20]>C1CCOC1.CCOC(C)=O.CO.O=C(O)O.Cl.[K+].[K+].N>[CH:1]#[C:2][c:3]1[cH:4][n:5][c:6]([NH:7][c:8]2[cH:9][c:10]([F:11])[cH:12][cH:13][cH:14]2)[n:15][c:16]1[NH:17][CH2:18][CH2:19][CH3:20]\"},\"mapped_reaction_smiles\":\"C[Si](C)(C)[C:1]#[C:2][c:3]1[cH:4][n:5][c:6]([NH:7][c:8]2[cH:9][c:10]([F:11])[cH:12][cH:13][cH:14]2)[n:15][c:16]1[NH:17][CH2:18][CH2:19][CH3:20]>C1CCOC1.CCOC(C)=O.CO.O=C(O)O.Cl.[K+].[K+].N>[CH:1]#[C:2][c:3]1[cH:4][n:5][c:6]([NH:7][c:8]2[cH:9][c:10]([F:11])[cH:12][cH:13][cH:14]2)[n:15][c:16]1[NH:17][CH2:18][CH2:19][CH3:20]\"}",
"reactionStep": {
"id": "sa_fb9584cb61f5472966300676",
"reactionHash": "483075fa6f534dc1ddc065ea47dcb3476c3c0436b81da05431bca647e6ddebf2"
},
"children": [
{
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"routeId": "sa_8e3f44fee898933583c9de3e",
"moleculeId": "sa_94dd8652da3a72f156bf7209",
"parentId": "12294",
"isLeaf": false,
"molecule": {
"id": "sa_94dd8652da3a72f156bf7209",
"inchikey": "MGZKROBWNTYBFZ-UHFFFAOYSA-N",
"smiles": "CCCNc1nc(Nc2cccc(F)c2)ncc1C#C[Si](C)(C)C"
},
"smiles": "CCCNc1nc(Nc2cccc(F)c2)ncc1C#C[Si](C)(C)C",
"reactionStepId": "sa_84f7dbb0d52a2808f594d372",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150045339A1;1459;1653020\",\"rsmi\":\"I[c:18]1[c:5]([NH:4][CH2:3][CH2:2][CH3:1])[n:6][c:7]([NH:8][c:9]2[cH:10][c:11]([F:12])[cH:13][cH:14][cH:15]2)[n:16][cH:17]1.[CH:19]#[C:20][Si:21]([CH3:22])([CH3:23])[CH3:24]>CCN(CC)CC.CCOC(C)=O.CN(C)C=O.Cl[Pd](Cl)([PH](c1ccccc1)(c1ccccc1)c1ccccc1)[PH](c1ccccc1)(c1ccccc1)c1ccccc1.Cl.[Cu]I.N>[CH3:1][CH2:2][CH2:3][NH:4][c:5]1[n:6][c:7]([NH:8][c:9]2[cH:10][c:11]([F:12])[cH:13][cH:14][cH:15]2)[n:16][cH:17][c:18]1[C:19]#[C:20][Si:21]([CH3:22])([CH3:23])[CH3:24]\"},\"mapped_reaction_smiles\":\"I[c:18]1[c:5]([NH:4][CH2:3][CH2:2][CH3:1])[n:6][c:7]([NH:8][c:9]2[cH:10][c:11]([F:12])[cH:13][cH:14][cH:15]2)[n:16][cH:17]1.[CH:19]#[C:20][Si:21]([CH3:22])([CH3:23])[CH3:24]>CCN(CC)CC.CCOC(C)=O.CN(C)C=O.Cl[Pd](Cl)([PH](c1ccccc1)(c1ccccc1)c1ccccc1)[PH](c1ccccc1)(c1ccccc1)c1ccccc1.Cl.[Cu]I.N>[CH3:1][CH2:2][CH2:3][NH:4][c:5]1[n:6][c:7]([NH:8][c:9]2[cH:10][c:11]([F:12])[cH:13][cH:14][cH:15]2)[n:16][cH:17][c:18]1[C:19]#[C:20][Si:21]([CH3:22])([CH3:23])[CH3:24]\"}",
"reactionStep": {
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"reactionHash": "f0862e9e1d2ff37b479020351eda6e9bbc00f4cadff2487e2298a244e21daae8"
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"children": [
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"routeId": "sa_8e3f44fee898933583c9de3e",
"moleculeId": "sa_95a9277ba0d873f43bb42b7f",
"parentId": "12295",
"isLeaf": true,
"molecule": {
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"inchikey": "CWMFRHBXRUITQE-UHFFFAOYSA-N",
"smiles": "C#C[Si](C)(C)C"
},
"smiles": "C#C[Si](C)(C)C",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
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},
{
"id": "12297",
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"moleculeId": "sa_086b352d7e8c09e03440c538",
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"molecule": {
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"inchikey": "JUTDWXACXMRPEG-UHFFFAOYSA-N",
"smiles": "CCCNc1nc(Nc2cccc(F)c2)ncc1I"
},
"smiles": "CCCNc1nc(Nc2cccc(F)c2)ncc1I",
"reactionStepId": "sa_114e5e0563cd476bf7f77dbb",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150045339A1;1032;1652937\",\"rsmi\":\"Cl[c:7]1[n:6][c:5]([NH:4][CH2:3][CH2:2][CH3:1])[c:18]([I:19])[cH:17][n:16]1.[NH2:8][c:9]1[cH:10][c:11]([F:12])[cH:13][cH:14][cH:15]1>CC1(C)C2CC[C@@]1(CS(=O)(=O)O)C(=O)C2.CN1CCCC1=O.O=C(O)O.[Na+]>[CH3:1][CH2:2][CH2:3][NH:4][c:5]1[n:6][c:7]([NH:8][c:9]2[cH:10][c:11]([F:12])[cH:13][cH:14][cH:15]2)[n:16][cH:17][c:18]1[I:19]\"},\"mapped_reaction_smiles\":\"Cl[c:7]1[n:6][c:5]([NH:4][CH2:3][CH2:2][CH3:1])[c:18]([I:19])[cH:17][n:16]1.[NH2:8][c:9]1[cH:10][c:11]([F:12])[cH:13][cH:14][cH:15]1>CC1(C)C2CC[C@@]1(CS(=O)(=O)O)C(=O)C2.CN1CCCC1=O.O=C(O)O.[Na+]>[CH3:1][CH2:2][CH2:3][NH:4][c:5]1[n:6][c:7]([NH:8][c:9]2[cH:10][c:11]([F:12])[cH:13][cH:14][cH:15]2)[n:16][cH:17][c:18]1[I:19]\"}",
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{
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"molecule": {
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"inchikey": "QZVQQUVWFIZUBQ-UHFFFAOYSA-N",
"smiles": "Nc1cccc(F)c1"
},
"smiles": "Nc1cccc(F)c1",
"reactionStepId": null,
"template": null,
"metadata": null,
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"children": []
},
{
"id": "12299",
"routeId": "sa_8e3f44fee898933583c9de3e",
"moleculeId": "sa_279f234d53f139eefab8131d",
"parentId": "12297",
"isLeaf": false,
"molecule": {
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"inchikey": "XRSARAODXOVBTQ-UHFFFAOYSA-N",
"smiles": "CCCNc1nc(Cl)ncc1I"
},
"smiles": "CCCNc1nc(Cl)ncc1I",
"reactionStepId": "sa_661eeb679957e61c88959fd2",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150045339A1;1029;1652936\",\"rsmi\":\"Cl[c:5]1[n:6][c:7]([Cl:8])[n:9][cH:10][c:11]1[I:12].[CH3:1][CH2:2][CH2:3][NH2:4]>C1CCOC1.CCN(C(C)C)C(C)C.CCOC(C)=O.O>[CH3:1][CH2:2][CH2:3][NH:4][c:5]1[n:6][c:7]([Cl:8])[n:9][cH:10][c:11]1[I:12]\"},\"mapped_reaction_smiles\":\"Cl[c:5]1[n:6][c:7]([Cl:8])[n:9][cH:10][c:11]1[I:12].[CH3:1][CH2:2][CH2:3][NH2:4]>C1CCOC1.CCN(C(C)C)C(C)C.CCOC(C)=O.O>[CH3:1][CH2:2][CH2:3][NH:4][c:5]1[n:6][c:7]([Cl:8])[n:9][cH:10][c:11]1[I:12]\"}",
"reactionStep": {
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"children": [
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